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Question 55

The major product of the following reaction is:

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  1. Aryl-Alkyl Ether Cleavage ($$\text{S}_{\text{N}}2$$):

    The methoxy oxygen ($$-\text{OCH}_3$$) attached to the benzene ring is protonated. Iodide ($$\text{I}^\ominus$$) attacks the methyl group via an $$\text{S}_{\text{N}}2$$ pathway, cleaving the alkyl $$\text{C--O}$$ bond to produce a phenol ($$-\text{OH}$$) group and iodomethane ($$\text{CH}_3\text{I}$$).


  2. Aliphatic Ether Cleavage ($$\text{S}_{\text{N}}1$$):

    The secondary aliphatic ether nitrogen-stabilized carbon center ($$-\text{CH}(\text{CN})--\text{O}--\text{CH}(\text{CH}_3)_2$$) undergoes protonation. Because it can form a highly stable, bulky tertiary carbocation ($$-\text{C}^\oplus(\text{CH}_3)_2$$) on the isopropyl side, the bond breaks via an $$\text{S}_{\text{N}}1$$ pathway to yield 2-iodopropane ($$\text{I--CH}(\text{CH}_3)_2$$) and a cyanohydrin intermediate ($$-\text{CH}(\text{CN})\text{OH}$$).


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